光致变色螺吲哚啉苯并吡喃的合成

Synthesis of photochromic 8'-nitro-6'-ethenyl-1,3,3-trimethyl spironindolinebenzopyan

目的 :设计并建立一种合成有光致变色性能的单体8 硝基 6 乙烯基 1 ,3,3 三甲基螺吲哚啉苯并吡喃的低成本 ,反应条件温和 ,操作简便的新方法 .方法 :水杨醛经氯甲基化 ,硝化 ,成磷盐后与甲醛起Witting反应得到 3 醛基 4 羟基 5 硝基苯乙烯 .2 ,3,3 三甲基吲哚甲基化后与氢氧化钠反应得Fischer碱 .所得Fischer碱与 3 醛基 4 羟基 5 硝基苯乙烯缩合得目标产物 .结果 :按起始原料计算 ,螺吲哚苯并吡喃单体的总产率为 2 1 .1 % .经熔点、元素分析、红外、核磁等方法鉴定 ,各中间体及目标产物均与其分子结构相符 .结论 :该合成方法所用原料价廉易得 ,反应条件温和 ,操作简便 ,总产率较文献大为提高 。

AIM: To develop a simple and economical new synthetic method of 8 nitro 6 ethenyl 1,3,3 trimethyl spirorindolinebenzopyan. METHODS: Salicylaldehyde was treated with chloromethylation,nitration and triphenyl phosphine,via “witting reaction” , to prepare 3 Aldehyde 4 hydroxy 5 nitro vinylbenzene. Fischer base obtained by 2,3,3 trimethyl 3 H indole was condensed with 3 Aldehyde 4 hydroxy 5 nitro vinylbenzene,the main product was 8 nitro 6 ethenyl 1,3,3 trimethyl spironindolinebenzopyan. RESULTS: Total yield of 8 nitro 6 ethenyl 1,3,3 trimethyl spirorindolinebenzopyan (caculated from the starting material saliaylaldehyde) was 21.1%. The structures of the intermediates and the monomer were confirmed by melting point, 1HNMR, IR and elemental analysis, and were in agreement with the corresponding molecular structures. CONCLUSION: Material of this new approach has advantages such as easier operation, low price and easy availability. The synthetic crafts are simple, convenient and beneficial to reducing the cost of the product.